2-Chloropyrimidine → HCID 67608326, compound

Participants

Reaction Conditions

Reaction Steps

A solution of amine 84 (325 mg, 0.59 mmol) in DMF (8 mL) was treated with 2-chloropyrimidine (88 mg, 0.76 mmol) and DIPEA (0.15 mL, 0.88 mmol) and heated to 80° C. in an oil bath. After 18 h, the reaction mixture was cooled to ambient temperature, diluted with water, and extracted with Et2O (3×). The combined organic extracts were washed successively with water (3×), and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 89 (341 mg, 92%) as an orange-colored solid that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ8.67 (d, J=4.8 Hz, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.30 (t, J=4.8 Hz, 1H), 7.08-6.87 (m, 1H), 6.86 (br s, 1H), 6.79-6.72 (m, 1H), 6.67-6.49 (m, 2H), 4.74-4.53 (m, 3H), 4.40-4.36 (m, 0.5H), 4.19-4.17 (m, 0.5H), 4.08-3.93 (m, 3H), 3.86-3.80 (m, 1H), 3.68-3.54 (m, 1H), 3.49-3.99 (m, 1H), 3.27-2.89 (m, 2H), 2.79 (s, 3H), 2.48-2.44 (m, 1.5H), 2.21-2.11 (m, 0.5H), 2.01-1.84 (m, 2H), 1.50-1.48 (m, 9H), 1.34-1.30 (m, 3H), 1.03-0.95 (m, 9H) ppm.

Provenance & Evidence